This invention generally pertains to heterocyclic carbon compounds having drug and bio-affecting properties and to their preparation and use. In particular, the invention is concerned with 1,4-disubstituted piperazine derivatives wherein the substituents are 2,4-thiazolidinedione-3-alkylenyl and aryl radicals as illustrated by the compound 3-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-2,4-thiazolidinedione.
Thiazolidinediones are known to the art. For example, Jones, et al., J. Chem. Soc., London, 91-92 (1946) refer to 5,5-dialkyl-2,4-thiazolidinedione barbituric acid analogs and disclose that an analogous spirothiazolidinedione (1) produced narcosis and analgesia in mice. ##STR1##
Various types of 1,4-substituted piperazine derivatives are also known to the art as illustrated in the following references.
Great Britain Application No. 2,023,594A discloses 1-(R-alkyl)-4-(3-trifluoromethylthiophenyl)piperazines useful for treating anxiety and depression having general formula (2) ##STR2## wherein n is 1-3 and R inter alia represents heterocycles such as ##STR3## wherein m is 0 or 1 and X is a --S--, --O--, imino, alkyl-imino or methylene.
Wu, U.S. Pat. No. 3,398,151, Wu, et al., U.S. Pat. No. 3,717,634 and, respective, corresponding Wu, et al., publications--J. Med. Chem., 12, 876-881 (1969), 15, 477-479 (1972)--variously describe psychotropic compounds resembling formula (3) ##STR4## wherein n is 4 or 5 and B inter alia represents phenyl plus various heterocycles (all with optional substituents): ##STR5##
Casten, et al., U.S. Pat. No. 4,182,763 concerns the anxiolytic use of compound (4) which is referred to in the biological literature as buspirone. ##STR6##
Palazzo, U.S. Pat. No. 3,857,845 describes the compound (5) as having typical tranquilizing properties. ##STR7##
None of the aforementioned references disclose or suggest piperazine derivatives containing the 2,4-thiazolidinedione heterocyclic component of the subject compounds of this invention.